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Holiday Rentals with Pools in Islamorada

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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    83 Matching Rentals in IslamoradaView all 162 rentals
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Luxury 3 BR condo, boatslip, easy accces to ocean1 / 19
    (5)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Come relax in Islamorada, the tropical jewel of the Florida Keys!!1 / 9
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2018
    It was perfect! Super clean, tasteful, & just the right size for what I needed! I absolutely loved it & would definitely stay again!!
    Reviewed 6 March 2018
    Tastefully decorated and very neat and clean. Comfortable throughout, beautiful setting & perfect to relax & get away from it all!!
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    About this property
    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 17
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    Great vacation. Received the much needed peace/quiet for rest that was well overdue. Room clean and relaxing. Visited Key West for a day trip while here and had a great time...
    Reviewed 2 June 2018
    The condo was fantastic, clean and with great facilities. The pool was excellent and fellow guest very friendly. The owner was in touch throughout our stay and could not have...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We are licensed in Islamorada:...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!1 / 30
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2018
    Simply an amazing condo. Location was perfect, made a great trip AMAZING. Owner was very accessible and friendly. Sunrise and set, along with the full moon views , just...
    Reviewed 28 April 2018
    Totally renevated condo with gorgeous views of ocean It was so nice to stay here! So cozyNice pool area! Co-owners were very friendly and made you feel at “home”Condo...
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. And new this year, a sandy beach. For two couples or a family with 2 kids. The two new extra long twin Pillow Top beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new Simmons Beautyrest Pillow Top...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed 18 January 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 14
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Beautiful view from the 3rd floor. Located away from US1 traffic so very quiet. Centrally located between Islamorada and Key Largo.
    Reviewed 15 August 2018
    This unit has it all, location, view and the perfect accommodations! We truly enjoyed ourselves and look forward to our next visit. Shelley was very responsive always making...
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    About this property
    This condo has been completely restored after Hurricane Irma’s d is now ready for guests to return. There is new drywall, paint, carpets and new furniture and is safe to stay in. Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    We stayed at Angler's Reef and had an amazing time. Jo was very helpful with the booking and very easy to work with. We felt like we were at home in her rental. She has...
    Reviewed 10 July 2017
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    **Winter Promo**  Modern Executive Bay Club Condo with Pool & Beach1 / 29
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    Reviewed 28 March 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Come and relax at our beautiful town home on...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores?  This home has everything - 4 bedroom, 4 bath home that has been updated.  The kitchen is amazing, suited for any type of entertaining.  The 3rd floor floor is a lofted master bedroom suite with a walk-in closet.  Two guest bedrooms are located on the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!1 / 15
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Luxury condo overlooking harbor with ocean view1 / 20
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    Luxurious surroundings, plush bath towels, great view, modern everything, cold central A/C, great soft pillow-top bed & nice quality linens. And, did I mention the...
    Reviewed 4 April 2018
    We are avid lovers of the keys and returned to vacation here about 20 times. We have stayed at Bay Harbor 3 times, but this condo is really superior. First, Lee is an...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    100' Private Beach Front Ocean Front Estate1 / 42
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    INCREDIBLE HOME ON THE BEACH!This beachfront home offered more amenities than any other home we have rented for vacation. Complete game room as well as kayaks and paddle...
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    FALL SPECIAL DISCOUNTED PRICING!!!1 / 70
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed 13 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental1 / 76
    (28)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish...
    Reviewed 28 March 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email me for the application. Weekly vacation rental...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE FULLY EQUIPPED KITCHEN WITH...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (15)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2018
    The condo is truly beautiful. We appreciated all the small amenities stocked within it and the furnishings and bed comfort was outstanding. The view was excellent and the staff...
    Reviewed 30 January 2018
    I was looking for place where my family could drink deeply of the “Keys Experience”. A place where we could fish either the ocean or back country, enjoy unbelievable sunsets...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbecue, front porch seating, balcony, and dock....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Location Information
    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys 33023
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Newly refinished  condo open water views very nice1 / 17
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    Besides the obvious gorgeous outdoor surroundings, this condo was equally as beautiful. It's hard to be inside when you're in the Keys, but Mark's condo makes it easy. The views...
    Reviewed 29 January 2017
    The condo was beautiful and well appointed. The community was beautiful with a great pool, nice beach, and extremely friendly people. Great restaurants and a cozy deli nearby...
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    About this property
    Beautiful professionally decorated superior condo in the best location in Islamorada. The unit is superior with the best water views, with everything you need ,full kitchen stocked with cookware, microwave, coffeemaker, large island counter, breakfast nook with ocean view, washer and dryer in...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed 25 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dubbed Aguazul, the home has four bedrooms and three bathrooms.  Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool, fish or swim from its dock, play in the sand of its private beach or merely sip a...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    **Winter Promo**  Family Friendly Executive Bay Townhome with Beach & Pool1 / 29
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous ocean views from every room. Built using ICF...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 24 April 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Ocean Views
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, balcony, and dock. Boat...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    BEACON REEF 3101 / 21
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Loved our stay in this beautiful condo! The view is spectacular! Condo is well stocked with all of your needs for a wonderful vacation in Islamorada!!! Highly recommend this...
    Reviewed 4 weeks ago
    Can't say enough great things about our stay at Beacon Reef 310!! From the moment you walk into the condo we knew we loved it, The whole place had that bright tropical feel...
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 310' is located in one of the most desirable condominium complexes in the Upper Keys. Convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BROCK HAUS ON THE GULF1 / 25
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Perfect location, perfect condo,and the best support team ever from Keys Holiday Rentals. I can't say enough about their commitment to making our vacation the best experience...
    Reviewed 28 August 2018
    We really had a great time. The view was awesome. Everything was as expected. The home was clean. Check in and check out was easy. We will stay again.
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    About this property
    Minimum Rental: 7 Days *Saturday to Saturday* 'Brock Haus on the Gulf' is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open water...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Internet Access
    • Air Conditioning
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the...
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    Location Information
    Islamorada, Florida Keys 34950
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 2141 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me...
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    About this property
    Minimum Rental: 28 Days 'The Palms #214' is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The PERFECT Escape with pool & jacuzzi1 / 22
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2 baths and there...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    MATECUMBE JEWEL1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Parking
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2017
    Very accommodating, house is well taken care of and lots of amenities. Just need to figure out how to stay longer.
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    About this property
    Minimum Rental: 28 Days 'Matecumbe Jewel' is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS 'Flamingo Cottage' is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #402' is a beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand NEW tennis court installed 2018! Situated right on the Atlantic Ocean in The Heart of Islamorada! Panoramic views of the water from almost every room, the main house has 3 bed/3baths. Guest cottage has 1bd/1ba. Nestled amongst lush tropical gardens and gated for total privacy. Take a morning...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #407' is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #405' is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    San Roc is a private home with 150 feet of oceanfront and spectacular views of open water with heated pool and spa. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acre secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as 'Millionaires Row' Enjoy...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    BEACON REEF 2221 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    We have so much enjoyed staying in this condo, Beacon Reef 222. The condo is very comfortable with a great kitchen and living area. The master bedroom is amazing with a large...
    Reviewed 13 July 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada....
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PALMS 4171 / 25
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #417' has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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